A personal milestone with my wife

Halloween! I know that for some of us this is a time to be able to take some initial steps outside in public without fear of ridicule, since guys dressed in feminine garb are just another part of this, to my mind, rather odd celebration.

I am a Brit living in the US, and in England when I was younger, Halloween had nothing like the popularity it does here. Trick or Treating did not exist when I was a kid, and at best some ghouls and ghosts got dressed up and very drunk at parties. Personally I never dressed to go out at Halloween any more than I did during the rest of the year.

Fast forward to now, and I am remarried to a gorgeous and complex woman here, and we have been together for 11 years. She found out about Laura by accident not long after we got together first, so has been aware of me for the duration. Having had one marriage fall apart, partly due to Laura, I have been very careful to not push things with my wife here. Altho she has been quite supportive for much of the time, I always felt it important to not make the same mistakes I had before, and we have grown together over the years to a fairly comfortable place.

Lately she has been talking more about us going out together with me dressed, and I had been waiting for the right time and opportunity for this. Halloween comes around. She had this idea for us to dress in costume as Donald and Melania, only she would be Donald and I would be Melania. I was cautiously enthusiastic about the idea, and started to make plans in my head as to what I could wear, as any woman would!

However, we had not decided for sure, and I did not get back from a work trip until later on Monday. We decided Monday night to go ahead with the plan and hit thrift stores to get suitable stuff Tuesday, altho of course I had some plans for stuff I already had, but which was probably completely unsuitable!

Dressing my wife as him was easy, but it got a little more difficult for Melania. We had some ups and downs in some of the stores, and then found a slightly more high end thrift place that had changing rooms and quite a large selection. My wife was really getting into it, and picked out a bunch of stuff for me to try. We had brought my breast forms, and I was wearing a bra and cincher under my shirt, so we could try things a little better. The ladies working in the store were getting into it too, and I soon found myself with an armful of stuff in the changing room.

Then I got disillusioned. None of these things were Laura, and were not suited to me, my body type, nor my taste! My wife had this white pant suit idea for Melania, which would not have been too bad if we had had time to find something that fit. We simply could not find anything that I felt good about, altho we did eventually get some white and slinky wide pants and a jacket that was a bit tight. We added a glittery top to go under, and then got a few trashy jewelry items. It was quite a first for us, with my wife joining me in the changing room and pushing and prodding, adjusting my boobs and such! I did feel a little 'man'handled tho!

My wife did say that this is what being female is about, and how that was why she hated going shopping for herself: she got disillusioned because she could rarely find something that she really liked. (This from a willowy 6 footer I should add! ) It was the first time she had started to think of me as female, at least in part, and treated me as such.

After the thrift store, we stopped at a couple of other places to add lashes, nails, another 'just in case' top, and some black strappy heels from Target that were pure Melania. She did not trust that I had any other suitable heels, but hey, I got another pair anyway! Then we finally went home to start the process of getting ready.

On the way home, she asked a bit more about what I did feel good wearing, and I told her most of my stuff was day wear, that I liked leggings and long sleeved tops. I also told her that I went out dressed sometimes to local stores and so on, and that surprised her a little I think. She asked if I changed my voice, and I said I did not have too much interaction when out, but if I did, that I tried to soften it a bit. She also asked about whether I had gone out on my trip to Vegas, and I truthfully told her no! She then asked if I ever tried to pick up guys when I was dressed and out, and again, I truthfully told her no. It was good to have an honest chat about things, and I felt close to her then. Usually when we had talked about dressing, one or other of us would have been discomfited, so this was good.

By now it was almost 4 pm, and as she went to a quick chiro appointment, I started to dress. She had said that I needed to tuck well so nothing showed thru the slinky pants, and I did. Usual gaff, panties and hose, then the pants. Nothing showed! Then the top, which was shedding glitter all over the place, and the wig. I thought I could just about pull this off without feeling too bad, but then tried the jacket. No way, it was just too tight and looked silly! When my wife got home, she checked me out and got me to try the jacket again. I was not having it altho she said it could work. She also hated my pantyhose under the pants and the strappy heels. It was getting a bit tricky, she had a different vision to me, and we went back and forth for some time, until she got disillusioned and said "well, we might as well just not bother at all..." and went into her office.

Oops! This was not going too great! I went in and we chatted again as she had cooled a little. (She is quite a volatile person, I think I said "complex"!) She apologized for her mini tantrum, and said she had realized that I was a woman who wanted to appear a woman, not as a caricature, and that the idea of me dressing as a woman, even as bit of a joke, was too close to the bone. I was too invested as Laura, and she totally understood. For her dressing as Donald was OK, no problem. This was a pretty cool observation I thought.

By this time, time was getting on, and we were back and forth whether we could still make it out as D & M. She said she really wanted to do my makeup, and that would be disappointing if she could not, but to do Melania I would still need a jacket. We tried a few alternatives, and then I tried a skirt I had, but she was dead set against me wearing pantyhose! She said I had great legs without, and that I should NEVER wear hose with open shoes! This goes against everything I thought, nylons have been a way to cover my beaten up legs from a life of knockabout, but she was adamant they were beautiful as they are. We will have to come back to that one!

We tried a lot of different combinations of things, but I just could not find anything that felt OK to me and that she did not feel strongly about. If we were going out, she wanted a say in what I was wearing too, and that was OK with me. I did put my heeled feet down that I needed to be comfortable too tho!

In the end, we ran out of time and got hungry, so we went out to eat anyway, just in drab. BUT, even tho disappointing that we did not get out as planned, we did learn a whole lot about each other, and a lot of avenues have been opened. Softly softly tho. I do not want to push too hard and go crazy. That could very well be counter-productive after gaining so much ground. I know we will be heading out together soon. She is actually out right now getting some rollers to be able to style my wigs!